Ethyl propionate at 185 K

Shallard-Brown, Howard A.; Watkin, David J.; Cowley, Andrew R.

doi:10.1107/s1600536805005271

Cited by 2 publications

(7 citation statements)

References 4 publications

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“…The low-temperature phase (Shallard-Brown et al, 2005) and the high-pressure phase (determined at 1.34, 1.98 and 2.45 GPa) have different symmetries; phase is tetragonal, space group P4 2 /mbc, and phase is monoclinic, space group P2 1 /c (the structures are compared in Fig. 3).…”

Section: Discussionmentioning

confidence: 99%

“…In the final cycles of the refinement the idealized methyl groups were allowed to rotate about the C-C bonds. Selected experimental and crystal data for C 5 H 10 O 2 in the high-pressure phase (this work), compared with the low-temperature phase after Shallard-Brown et al (2005). Computer programs used: CrysAlis (Oxford Diffraction, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1990).…”

Section: Figurementioning

confidence: 99%

“…180.0 176.2 7175.1 (4) 175.3 (4) † Average values of disordered molecule after Shallard-Brown et al (2005). Table 3 Selected molecular dimensions (Å , ) of ethyl propionate in phase at 0.1 MPa and 185 K (Shallard-Brown et al, 2005), and in phase (this work).…”

Section: Ep Compressionmentioning

confidence: 99%

“…We have now studied the structure of ethyl propionate, C 5 H O 2 (denoted EP). It is liquid at normal conditions, and below 199 K it crystallizes in the tetragonal space group P4 2 /mbc, with the molecules disordered orientationally in two positions (Shallard-Brown et al, 2005). Ethyl propionate is an intriguing compound used in the flavours and fragrances industry.…”

Section: Introductionmentioning

confidence: 99%

“…Ethyl propionate is an intriguing compound used in the flavours and fragrances industry. Many ketones and esters are liquids at room temperature, and ethyl propionate was chosen by Shallard-Brown et al (2005) as a representative of these compounds for structural analysis of the crystal in-situ frozen at 185 K. The EP molecule consists of five rotor fragments; however, its conformation is extended and planar in the low-temperature structure, denoted phase . The symmetry of the EP molecule is lower than the C 2h -symmetric special site it occupies in the phase at 185 K, the most distinct element of this molecularshape asymmetry being the carbonyl O atom (Fig.…”

Section: Introductionmentioning

confidence: 99%

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In-situ high-pressure study of the ordered phase of ethyl propionate

Gajda

Katrusiak

2007

Acta Crystallogr Sect B

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Ethyl propionate, C5H10O2 (m.p. 199 K), has been in-situ pressure-frozen and its structure determined at 1.34, 1.98 and 2.45 GPa. The crystal structure of the new high-pressure phase (denoted beta) is different from phase alpha obtained by lowering the temperature. The freezing pressure of ethyl propionate at 296 K is 1.03 GPa. The molecule assumes an extended chain s-trans-trans-trans conformation, only slightly distorted from planarity. The closest intermolecular contacts in both phases are formed between carbonyl O and methyl H atoms; however, the ethyl-group H atoms in phase beta form no contacts shorter than 2.58 A. A considerable molecular volume difference of 24.2 A3 between phases alpha and beta can be rationalized in terms of degrees of freedom of molecules arranged into closely packed structures: the three degrees of freedom allowed for rearrangements of molecules confined to planar sheets in phase alpha, but are not sufficient for obtaining a densely packed pattern.

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Section: Discussionmentioning

confidence: 99%

Section: Figurementioning

confidence: 99%

Section: Ep Compressionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

In-situ high-pressure study of the ordered phase of ethyl propionate

Gajda

Katrusiak

2007

Acta Crystallogr Sect B

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Crystal packing and melting temperatures of small oxalate esters: the role of C—H...O hydrogen bonding

Joseph

Ranganathan

Mahapatra

et al. 2011

Acta Crystallogr Sect B

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The simple dialkyl oxalates are generally liquids at room temperature except for dimethyl and di-tert-butyl oxalate which melt at 327 and 343 K. The crystal structures of diethyl, di-iso-propyl, di-n-butyl, di-tert-butyl and methyl ethyl oxalates were determined. The liquid esters were crystallized using the cryocrystallization technique. A comparison of the intermolecular interactions and packing features in these crystal structures was carried out. The crystal structure of dimethyl oxalate was redetermined at various temperatures. The other compounds were also studied at several temperatures in order to assess the attractive nature of the hydrogen bonds therein. A number of moderate to well defined C-H···O interactions account for the higher melting points of the two solid esters. Additionally, a diminished entropic contribution ΔS(m) in di-tert-butyl oxalate possibly increases the melting point of this compound further.

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Ethyl propionate at 185 K

Abstract: The title compound, C5H10O2, was prepared by a modified zone‐refining technique, and has a layered structure with a high degree of disorder within the layers.

Cited by 2 publications

References 4 publications

In-situ high-pressure study of the ordered phase of ethyl propionate

In-situ high-pressure study of the ordered phase of ethyl propionate

Crystal packing and melting temperatures of small oxalate esters: the role of C—H...O hydrogen bonding

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